5-nitro-2-furaldehyde semioxamazone



Patented Feb. 18, 1947 I UNITED STATES PATENT OFFICE 5-NITRO-2-FURALDEHYDE SEMIOXAMAZON E William B. Stillman and Albert B. Scott, Norwich, N. Y., assignors, by mesne assignments, to Eaton Laboratories, Inc., Norwich, N. Y., a corporation of New York No Drawing. Original application August 28,

1945, Serial No. 613,205. Divided and this application October 25, 1946, Serial No. 705,795

1 Claim. (01. 260345) 1 2 This invention relates to a new chemical comalate according to the directions of Weddigo, J. pound, 5-nitro-2-furaldehyde semioxamazone, Prakt. Chem, (2), 10, 196 (1874). SemioXamadescribed by the formula: zide is then prepared from this product by the method of Kerp and Unger, Ber. 30, 586 (1897). k H To a solution of '7 g. of the latter compound in 01M QH= 1 T hot water, is added, slowly with stirring, 9 55 g.

0 of nitrofurfural in ethanol. The mixture 1s al- CONH lowed to cool and the tan solid is removed by We have made e discovery that this new filtration. Purification is efiected by suspending P un While Sharing the antiseptic p opert s 10 the product in warm dioxane, then allowing the whlch are common to many nitrofurans, is (115- mixture to cool. The solid is again removed by tlnglllshed from most other trofurans by its filtration. It is light yellow, microcrystalline, effectiveness against infections when adminisweighs 11,6 (76%); M. P, 250; solubility in tered orally. In doses well below the toxic limit, water, 200,000, it has proved highly efiective in the treatment Thi application is a division of our appli Of Streptococcus a 'YD infections, and tion Serial No. 613,205, filed August 28, 1945, as

s a V ua e chemothgrapeutic agent/- a continuation-in-part of our applications filed e n Compound 13 m e as follows: it May 17, 1944, and bearing Serial Nos. 536,046, 0000211, 000cm; CONHNH; 536,047 and 536,048.

6000,13 B (QONHQ What is claimed is:

5-n1tro-2-furaldehyde sem1oxamazone represented by the formula:

Oxalic ester amide is prepared from ethyl ox- 

